For his family, Jackson Holliday’s debut brings a flood of emotions, and a sense of history repeating

The emotional response has never left Tom Holliday, even after 20 years. He wasn’t there — as the pitching coach for the University of Texas, he stayed back for his own baseball game — but there on the television, on April 16, 2004, Matt Holliday donned a Colorado Rockies uniform and walked onto the field as a Major League Baseball player.

There’s no replicating that feeling, the flood of tears, the pride and joy in knowing your son had achieved his lifelong dream.

So, when it’s Jackson Holliday’s turn to stride onto the Fenway Park grass Wednesday evening with a Baltimore Orioles uniform on, Tom Holliday will turn to his son, Matt. He will watch for a similar reaction because he knows what will occur.

There’s pride for a grandfather in seeing his grandson make it to The Show. But for a father?

“I’m just going to watch to see his reaction,” Tom Holliday said Wednesday afternoon. “I want to see a 6-foot-4, 250-pound guy who played 15 years feel the emotion of having your kid out there.”

On Wednesday night in Boston, Leslee Holliday will experience many of the same emotions she did nearly 20 years ago. This time, however, a baby Jackson won’t be in her arms to watch her husband play; Jackson will be on the field.

All those years ago, Leslee said, “ignorance was bliss.” They didn’t know what to expect heading into a 15-year MLB career. But now they do — they understand how few people make it to this point.

“With Matt it was, ‘Oh, this is fun,’” Leslee Holliday said. “And with Jackson, we’re like, ‘Oh my gosh, this is amazing.’”

This rush isn’t new to either Leslee or Tom Holliday, even though Tom waited to see his son play in person until the Longhorns’ 2004 season ended in the finals of the College World Series. He ran to watch Matt Holliday’s next game, thinking the whole time that Matt was a kid among grown men.

Then he realized they were all kids out there; Matt would fit in just fine. Tom’s nerves settled. He soaked in the roar of the crowd when his son came through for the Rockies.

“When the crowd buys into your kid, that is the most satisfying feeling I can describe,” Tom Holliday said. “And Colorado, I mean, shoot, they had an experienced club and then here comes Matt. Matt had a really good year, and standing ovations for the rookie when you’ve got Larry Walker and Todd Helton?”

It was magical. Between the recruiting trips for Texas, Tom Holliday spent that summer and fall immersed in his son’s career. “I wanted to go to Colorado all the time,” he said. “Whenever we had a chance, I went to Colorado.”

Now it’s his grandson’s turn. And it’s Tom Holliday’s son’s turn to immerse himself in the nerves and joy that accompany Jackson Holliday’s burgeoning career.

On Tuesday night, the family was all together in Stillwater, Oklahoma, watching Ethan Holliday’s baseball game. The younger brother of Jackson, Ethan is expected to be another high draft pick. Tom Holliday drove home and turned on Oklahoma State baseball — his former team, and the club his other son, Josh, coaches. And midway through that game, Matt called his dad to tell him the news: Jackson would be on his way to Boston.

The next two hours, then, were a whirlwind of travel accommodations to ensure the family would be there at Fenway Park. They boarded a predawn flight to Boston on Wednesday and landed in time to have lunch with Jackson. Then they prepared to go to the ballpark, seeing their 20-year-old son and grandson at the highest level.

Almost 20 years to the day, Jackson will follow in his father’s footsteps, making his debut in April.

“We kept saying, ‘Dang, this is déjà vu.’ It’s almost the exact same time,” Tom Holliday said.

When that call arrived, memories began to flood Leslee’s mind. She thought back to a video she recorded when Jackson Holliday was a kindergartener. The question posed that day for the class: “What do you want to be when you grow up?”

There was Jackson, in a full Cardinals uniform.

“He was dressed like Matt,” Leslee said. “And he stood there very confidently as a little guy and said, ‘I want to be like my dad. I want to be a Major League Baseball player someday.’ So, when you get the phone call like we received yesterday, and him saying ‘I’m going, I’m going to be in Boston,’ all of those little memories come flooding back in your mind, of the moments when he said this is what I want to do when I grow up.”

“He’s wanted to do this for as long as I can remember,” Matt Holliday said after he and Ethan stood talking with Jackson’s new teammates during batting practice. “It’s always more fulfilling to watch your kids achieve things than yourself.”

Leslee and Matt saw Jackson’s work ethic back up his long-held desire.

The similarities between Matt and Jackson continue with their offseason workouts prior to receiving a promotion. Before reporting to spring training in 2004, Matt Holliday worked out with the Texas Longhorns. Tom had never seen his son so motivated. He reached a higher level of training, and by the time he departed for camp, “it was the best I’ve ever seen him hit a baseball.”

Watching Jackson Holliday this winter evoked a similar memory. Tom Holliday told his wife, Kathy, “he’s not going to be in Triple-A very long.”

Matt played six Triple-A games in 2004 before he got the call to join Colorado. Jackson played 10 Triple-A games this year before receiving the call to join the Orioles.

There is a difference for Tom, however, in all this. The nerves that enveloped him for Matt’s debut aren’t there this time. He knows how well Matt prepared Jackson for this moment. Matt has counseled his son on what it’s like to play in the majors, and Jackson followed his dad through major league clubhouses growing up.

“Matt’s been with Jackson,” Tom Holliday said. “It’s been kind of fun to watch, and that’s a real advantage, especially when somebody’s done it for 15 years. So Jackson had an edge over his dad.”

“Matt’s spirit is with him,” Tom Holliday added. “When you watch it as a grandpa, you just kind of sit there and go, ‘I don’t need to worry about telling him what to do and what not to eat. I don’t need to tell him to go get your rest.’ He knows that.”

The family will sit down inside Fenway Park on Wednesday night, looking out at a field for a second debut. First it was Matt, 20 years ago. Now it’s Jackson. In the time between, Matt played just over 1,900 games.

But nothing will be like the first.

“I’m sure it will be emotional, and it was emotional for me to watch Matt play as well,” Leslee said. “It’s a sweet gift and something I don’t take for granted, that these two men that I love have had an opportunity to fulfill a lifelong dream.”

Andy Kostka

andy.kostka@thebaltimorebanner.com

Andy Kostka is an Orioles beat writer for The Baltimore Banner. He previously covered the Orioles for The Baltimore Sun. Kostka graduated from the University of Maryland and grew up in Rockville.

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